Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 17, Pages 3265-3274Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200222
Keywords
asymmetric catalysis; heterogeneous catalysis; immobilization; mesoporous materials; Michael addition
Categories
Funding
- China National Natural Science Foundation [20673072]
- Shanghai Sciences and Technologies Development Fund [10DJ1400103, 10JC1412300, 12nm0500500]
- Shanghai Municipal Education Commission [12ZZ135, S30406]
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A periodic mesoporous organosilica (PMO) with chiral cyclohexyldiamine-based nickel(II) complexes incorporated within the silica framework was prepared through a co-condensation of (1R,2R)-cyclohexyldiamine-derived silane and Ph-bridged silane followed by complexation of nickel(II) bromide in the presence of (1R,2R)-N,N'-dibenzylcyclohexyldiamine. Structural analyses by X-ray powder diffraction, nitrogen sorption and transmission electron microscopy disclosed its orderly mesostructure while characterization by solid-state NMR and X-ray photoelectron spectroscopy demonstrated the well-defined single-site chiral bis(cyclohexyldiamine)-based nickel(II) active centers incorporated within the PMO material. In particular, as a heterogeneous chiral catalyst, this periodic mesoporous organosilica showed high catalytic activity and excellent enantioselectivity in asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroalkenes (more than 92% conversions and up to 99% ee values). More importantly, this heterogeneous catalyst could be recovered easily and reused repeatedly nine times without obviously affecting its ee value, showing good potential for industrial applications.
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